A kind of biguanide compound and its preparation method and application

A compound, biguanide technology, applied in the field of medicine, can solve the problem of lack of treatment methods and drugs

Inactive Publication Date: 2017-07-18
SHANGHAI RENLI PHARMA SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The pathogenesis of alcoholic and non-alcoholic fatty liver disease has not been fully elucidated, so there is still a lack of effective treatment methods and drugs

Method used

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  • A kind of biguanide compound and its preparation method and application
  • A kind of biguanide compound and its preparation method and application
  • A kind of biguanide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Embodiment 1: Synthesis of RL-66102

[0102] In a 100ml round bottom bottle, add metformin hydrochloride 4g (24mmol), dichloromethane 50ml, add 25% sodium hydroxide 40ml, stir, after clarification, add potassium iodide 3 small grains, then add dropwise 3-bromopropene 2.9g / 2.1ml (24mmol), dripped in about 10 minutes, stirred magnetically, and ran the plate after 1 hour (developing agent: dichloromethane:methanol:formic acid=4.3:0.7:3dr). A total of 20 hours of reaction, post-processing. The reaction solution was transferred to a separatory funnel, and the dichloromethane and aqueous phase were separated. The aqueous phase was extracted three times with 20 ml of dichloromethane each time. The dichloromethane liquids were combined, and the dichloromethane was evaporated to dryness to obtain 2.3 g of crude oil. The crude product was subjected to column chromatography on 100-200 mesh silica gel (mobile phase: dichloromethane:methanol=900:100) to obtain 0.75 g of the crude...

Embodiment 2

[0103] Embodiment 2: Synthesis of RL-66106

[0104] In a 100ml round bottom bottle, add metformin hydrochloride 2g (12mmol), dichloromethane 25ml, ice bath, add 25% sodium hydroxide 10ml and stir, then add bromooctane 2.31g (12mmol), potassium iodide 3 pellets, magnetic Stirring, room temperature, a total of 30 hours of reaction, post-processing. The reaction solution was transferred to a separatory funnel, and the dichloromethane and aqueous phase were separated. The aqueous phase was extracted three times with 20 ml of dichloromethane each time. The dichloromethane liquids were combined, and the dichloromethane was evaporated to dryness to obtain 1.6 g of crude oil. The crude product was subjected to column chromatography on 100-200 mesh silica gel (mobile phase: dichloromethane:methanol=900:100) to obtain 0.95 g of the crude product of the target product. Reverse-phase separation was performed on a medium-pressure column, mobile phase: water / acetonitrile=98 / 2, and 0.45 g...

Embodiment 3

[0105] Embodiment 3: Synthesis of RL-66110

[0106] In a 100ml round bottom bottle, add metformin hydrochloride 2g (12mmol), dichloromethane 25ml, ice bath, add 25% sodium hydroxide 10ml, stir, after clarification, add benzyl bromide 2.05g (12mmol), potassium iodide 3 pellets, magnetic Stirring, room temperature, a total of 18 hours of reaction, post-processing. A solid was seen in the reaction flask, which was filtered, washed with 2 ml of dichloromethane, and dried to obtain 0.9 g of a colorless solid. The solid was heated and dissolved in 150 ml of acetonitrile, filtered, left to cool, and crystallized to obtain 0.42 g of a colorless solid. Yield 16.0%. The proton nuclear magnetic spectrum data of product are: 1 H NMR (600MHz, DMSO) δ7.29(d, J=7.5Hz, 2H), 7.23(t, J=7.6Hz, 2H), 7.11(t, J=7.3Hz, 1H), 5.21(s, 4H ), 4.17 (s, 2H), 2.78 (s, 6H). HRMS [M+H] 220.35.

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Abstract

The invention relates to bis-biguanide. The structure formula I of the bis-biguanide is as shown in figure, wherein R is one of H, C1-10 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 alkyl sulphanyl, C1-6 carbonyl, C1-6 carbalkoxy, carbonyl amino, substitutional carbonyl amino, sulfonyl amino, phenyl, substitutional phenyl, naphthenic base, substitutional naphthenic base, heterocycle naphthenic base, substitutional heterocycle naphthenic base, ceteroary or substitutional cateroary. The invention further provides a preparation method of the bis-biguanide, monocrystal of partial compound and application of the bis-biguanide. Via animal experiment, alcoholic or non-alcoholic fatty liver disease is alleviated remarkably, and the bis-biguanide can be used for treatment of alcoholic or non-alcoholic fatty liver disease and relevant diseases thereof.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a biguanide compound, a preparation method thereof, and an application in the treatment of alcoholic or nonalcoholic fatty liver. Background technique [0002] Clinically, fatty liver is divided into alcoholic fatty liver disease and non-alcoholic fatty liver disease according to whether excessive drinking for a long time. Alcoholic fatty liver disease (English name is alcohol fatty liver disease, referred to as AFLD), which refers to the accumulation of lipid in the liver cells caused by excessive drinking of ethanol for a long time, which exceeds 5% of the wet weight of the liver, or In histology, more than one-third of the liver cells per unit area undergo fatty degeneration, which is clinically manifested as fat deposition in the liver cells. In severe cases, it can cause alcoholic hepatitis, alcoholic liver fibrosis, and alcoholic liver cirrhosis. Even induce liver cancer....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/26C07C277/08C07C277/06A61K31/155A61P1/16A61P35/00
Inventor 不公告发明人
Owner SHANGHAI RENLI PHARMA SCI & TECH
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